US4240949A - Polymeric compositions and process for their production - Google Patents
Polymeric compositions and process for their production Download PDFInfo
- Publication number
- US4240949A US4240949A US05/951,588 US95158878A US4240949A US 4240949 A US4240949 A US 4240949A US 95158878 A US95158878 A US 95158878A US 4240949 A US4240949 A US 4240949A
- Authority
- US
- United States
- Prior art keywords
- sulfur
- compositions according
- modified
- employed
- percent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 25
- 238000000034 method Methods 0.000 title claims abstract description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 39
- 239000011593 sulfur Substances 0.000 claims abstract description 38
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 38
- -1 nitrogen-containing compound Chemical class 0.000 claims abstract description 22
- 239000004014 plasticizer Substances 0.000 claims abstract description 15
- 150000003463 sulfur Chemical class 0.000 claims abstract description 9
- 150000001412 amines Chemical class 0.000 claims abstract description 4
- 150000001408 amides Chemical class 0.000 claims abstract description 3
- 229920000642 polymer Polymers 0.000 claims description 17
- 239000004743 Polypropylene Substances 0.000 claims description 8
- 229920001155 polypropylene Polymers 0.000 claims description 8
- 239000006185 dispersion Substances 0.000 claims description 5
- 239000004698 Polyethylene Substances 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 229920000573 polyethylene Polymers 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 3
- 230000000996 additive effect Effects 0.000 claims description 3
- 239000000945 filler Substances 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 229920000098 polyolefin Polymers 0.000 claims description 3
- 238000010526 radical polymerization reaction Methods 0.000 claims description 3
- 239000003086 colorant Substances 0.000 claims description 2
- 150000004985 diamines Chemical class 0.000 claims description 2
- 239000002270 dispersing agent Substances 0.000 claims description 2
- 239000003995 emulsifying agent Substances 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 229910052945 inorganic sulfide Inorganic materials 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 239000000454 talc Substances 0.000 claims 1
- 229910052623 talc Inorganic materials 0.000 claims 1
- 239000004033 plastic Substances 0.000 description 5
- 229920003023 plastic Polymers 0.000 description 5
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 3
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 description 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- DZDVMKLYUKZMKK-UHFFFAOYSA-N 7-methyloctan-1-amine Chemical compound CC(C)CCCCCCN DZDVMKLYUKZMKK-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- VKCLPVFDVVKEKU-UHFFFAOYSA-N S=[P] Chemical class S=[P] VKCLPVFDVVKEKU-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- ZOLLIQAKMYWTBR-RYMQXAEESA-N cyclododecatriene Chemical compound C/1C\C=C\CC\C=C/CC\C=C\1 ZOLLIQAKMYWTBR-RYMQXAEESA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 229940043237 diethanolamine Drugs 0.000 description 1
- 238000006253 efflorescence Methods 0.000 description 1
- LDLDYFCCDKENPD-UHFFFAOYSA-N ethenylcyclohexane Chemical compound C=CC1CCCCC1 LDLDYFCCDKENPD-UHFFFAOYSA-N 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 206010037844 rash Diseases 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/02—Elements
- C08K3/06—Sulfur
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0016—Plasticisers
Definitions
- the present invention relates to polymeric compositions, in particular dispersions, of sulfur and polymers, in particular polyolefins, preferably polyethylene and polypropylene, obtained by radical polymerization or additive reaction.
- U.S. Pat. No. 3,450,667 describes a polymeric product extended (filled) with 10 to 45 percent by weight of sulfur.
- elementary sulfur and solid polymer are heated to about 190° to 218° C. until the sulfur is present in amorphous, polymeric form.
- polymeric compositions according to the invention are thus characterized in that they contain 10 to 90 percent by weight, preferably 20 to 60 percent by weight, of sulfur modified by the addition of plasticizers optionally containing at least one viscosity regulator.
- Suitable polymeric components are particularly polyolefins, preferably polyethylene or polypropylene, but also polymers obtained by polymeric addition such as epoxy and polyurethane products.
- Suitable plasticizers are olefinic hydrocarbons such as dicyclopentadiene, styrene, cyclooctadiene, cyclododecatriene, dipentene, vinyl cyclohexane or inorganic sulfides such as arsenic sulfides and phosphor sulfides.
- the plasticizers are preferably present in the polymeric composition in amounts of 1 to 20 percent by weight based on sulfur.
- a viscosity regulator optionally in the form of a thiophilic, nitrogen-containing compound, can be added to the sulfur.
- Thiophilic, nitrogen-containing compounds are, a.o., amines, diamines, alkanol amines and amides, e.g.
- primary, secondary and tertiary amines such as butylamine, dibutylamine or tributylamine; aliphatic straight-chained, branched or cyclic amines such as n-butylamine, isononylamine and cyclohexylamine; tetramethyl ethylene diamine, diethanol amine; aromatic amines such as aniline and naphthylamine, fatty acid amides and ureas; and heterocyclic amines such as piperidine and benzothiazoles.
- the viscosity of the sulfur can be regulated and the degree of polymerization of the sulfur thus brought to an optimum.
- the thiophilic, nitrogen-containing compound is preferably used in amounts of up to 5 percent by weight based on sulfur.
- the sulfur can contain fillers, dispersing agents, emulsifiers, colorants and/or the inhibibors conventionally used in the processing of plastic materials.
- the invention further relates to a process for the production of the polymeric compositions which is characterized in that the sulfur is treated, prior to admixture to the polymeric compound, with plasticizers optionally containing viscosity regulators.
- the polymeric compositions can be produced by mixing of the components at temperatures of 120° to 200° C. and dispersing, kneading, extruding or the like.
- the dispersions can be produced by disperging the sulfur in the polymeric substance or vice versa.
- the products according to the invention are used in the plastics industry for conventional purposes or as coating materials.
- the polymers extended (filled) with sulfur show improved physical properties such as better impact strength, tensile strength and elongation at break as compared to the pure polymeric product.
- 500 g sulfur modified by means of 5 percent by weight of dicylcopentadiene are pulverized, premixed with 500 g granules of isotactic polypropylene died black and then filled through a hopper into an injection molding machine with screw conveyor.
- the temperature of the cylinder is 180° C. in zones 1 and 2 and 150° C. in zone 3. After 15 seconds, a molded article of metallic color and high strength can be taken from the mold.
- a three-necked flask provided with agitator and reflux cooler is charged with 450 g sulfur and 50 g cyclopentadiene, the reaction is continued for 4 hours at 140° C.
- the modified sulfur is then transferred to a beaker preheated to 150° C.
- 48 g atactic polypropylene in small pieces are added and dispersion is carried on for 5 minutes by means of a high-speed mixer (Ultraturrax).
- 137 g filler (trade name Plastorit Naintsch) of a particle size of 20 ⁇ was stirred in and the mixture is poured onto a concrete surface. After one hour, the coating shows good adhesion to concrete and high strength.
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Disclosed is an olefinic, polymeric composition and a method for making such polymeric composition wherein the composition includes 10%-90% modified sulfur. The sulfur is modified by the addition of at least one plasticizer and a thiophilic, nitrogen-containing compound as a viscosity regulator. In accordance with the invention, elemental sulfur is modified by the addition of any of several plasticizers in amounts of about 1%-20% by weight based on sulfur and the addition of up to about 5% by weight of a thiophilic, nitrogen-containing compound such as any of various amines or amides.
Description
The present invention relates to polymeric compositions, in particular dispersions, of sulfur and polymers, in particular polyolefins, preferably polyethylene and polypropylene, obtained by radical polymerization or additive reaction.
It is known to incorporate sulfur in small percentages into polymers, as this improves the strength properties of the polymers and allows extending (filling) expensive plastic materials by inexpensive sulfur.
U.S. Pat. No. 3,450,667 describes a polymeric product extended (filled) with 10 to 45 percent by weight of sulfur. In producing the polymeric composition, elementary sulfur and solid polymer are heated to about 190° to 218° C. until the sulfur is present in amorphous, polymeric form.
According to Japanese patent specification No. 7390342, sulfur is mixed with polypropylene, the sulfur concentration amounting to a maximum 30%. At concentrations in excess of this, the sulfur effloresces. For this reason, U.S. Pat. No. 3,450,667 describes the processing of polymers consisting of α-olefins with sulfur at temperatures >190° C. in devices conventional for the plastics processing industries, such as extruders, mills, kneaders, whereby the polymeric sulfur obtained at these high temperatures can be mixed with the polymers in high concentrations without separation.
It was surprisingly found that polymers can be extended (filled) with larger amounts of sulfur without efflorescences if the sulfur added to the polymer had previously been treated with plasticizers.
The polymeric compositions according to the invention are thus characterized in that they contain 10 to 90 percent by weight, preferably 20 to 60 percent by weight, of sulfur modified by the addition of plasticizers optionally containing at least one viscosity regulator.
Suitable polymeric components are particularly polyolefins, preferably polyethylene or polypropylene, but also polymers obtained by polymeric addition such as epoxy and polyurethane products.
Suitable plasticizers are olefinic hydrocarbons such as dicyclopentadiene, styrene, cyclooctadiene, cyclododecatriene, dipentene, vinyl cyclohexane or inorganic sulfides such as arsenic sulfides and phosphor sulfides.
The plasticizers are preferably present in the polymeric composition in amounts of 1 to 20 percent by weight based on sulfur.
In addition to the plasticizer, a viscosity regulator, optionally in the form of a thiophilic, nitrogen-containing compound, can be added to the sulfur. Thiophilic, nitrogen-containing compounds are, a.o., amines, diamines, alkanol amines and amides, e.g. primary, secondary and tertiary amines such as butylamine, dibutylamine or tributylamine; aliphatic straight-chained, branched or cyclic amines such as n-butylamine, isononylamine and cyclohexylamine; tetramethyl ethylene diamine, diethanol amine; aromatic amines such as aniline and naphthylamine, fatty acid amides and ureas; and heterocyclic amines such as piperidine and benzothiazoles.
By means of these viscosity regulators, the viscosity of the sulfur can be regulated and the degree of polymerization of the sulfur thus brought to an optimum.
The addition of sulfur in polymeric form permits maintaining the dispersion up to setting of the product, which allows the production of a polymeric product of high sulfur content without separation.
The thiophilic, nitrogen-containing compound is preferably used in amounts of up to 5 percent by weight based on sulfur.
In addition to the plasticizers, the sulfur can contain fillers, dispersing agents, emulsifiers, colorants and/or the inhibibors conventionally used in the processing of plastic materials.
The invention further relates to a process for the production of the polymeric compositions which is characterized in that the sulfur is treated, prior to admixture to the polymeric compound, with plasticizers optionally containing viscosity regulators.
The advantage over known processes achieved according to the invention resides in the fact that it is not necessary to first produce polymeric sulfur by exposure to high temperatures, but instead the polymeric sulfur is obtained by means of the plasticizers mentioned and then incorporated into the polymers.
The polymeric compositions can be produced by mixing of the components at temperatures of 120° to 200° C. and dispersing, kneading, extruding or the like.
The dispersions can be produced by disperging the sulfur in the polymeric substance or vice versa.
The products according to the invention are used in the plastics industry for conventional purposes or as coating materials.
The polymers extended (filled) with sulfur show improved physical properties such as better impact strength, tensile strength and elongation at break as compared to the pure polymeric product.
The products are also economically significant, since expensive plastic materials can be partially replaced by inexpensive sulfur.
The invention is explained in detail by means of the following examples:
Into 1200 g of the liquid sulfur, 72 g dicyclopentadiene are poured under the surface and 1.2 g dibutyl amine are added at 140° C. and under stirring. After 4 hours mixing time, the modified sulfur is added to 2100 g atactic polypropylene melted at 170° C. and mixed in a Hobart mixer with kneading hook for 15 minutes. The result is a homogenous, elastic product which is poured into a glass mold sprayed with mold release.
500 g sulfur modified by means of 5 percent by weight of dicylcopentadiene are pulverized, premixed with 500 g granules of isotactic polypropylene died black and then filled through a hopper into an injection molding machine with screw conveyor. The temperature of the cylinder is 180° C. in zones 1 and 2 and 150° C. in zone 3. After 15 seconds, a molded article of metallic color and high strength can be taken from the mold.
A three-necked flask provided with agitator and reflux cooler is charged with 450 g sulfur and 50 g cyclopentadiene, the reaction is continued for 4 hours at 140° C. The modified sulfur is then transferred to a beaker preheated to 150° C. Then, 48 g atactic polypropylene in small pieces are added and dispersion is carried on for 5 minutes by means of a high-speed mixer (Ultraturrax). Then, 137 g filler (trade name Plastorit Naintsch) of a particle size of 20μ was stirred in and the mixture is poured onto a concrete surface. After one hour, the coating shows good adhesion to concrete and high strength.
Claims (14)
1. Polymeric compositions of olefinic polymers obtained by radical polymerization or additive reaction, characterized in that they contain 10 to 90 percent by weight of sulfur modified by means of at least one plasticizer and a thiophilic, nitrogen-containing compound as a viscosity regulator.
2. Compositions according to claim 1, wherein the polymer is dispersed in said modified sulfur as a carrier.
3. Compositions according to claim 1, wherein the polyolefin employed is polyethylene or polypropylene.
4. Compositions according to claim 1, characterized in that they contain 20 to 60 percent by weight of modified sulfur.
5. Compositions according to claim 1, wherein the plassticizer is employed in an amount of 1 to 20 percent by weight based on sulfur.
6. Compositions according to claim 5, wherein the plasticizer employed is an olefinic hydrocarbon.
7. Polymeric compositions according to claim 1, wherein the plasticizer employed is an inorganic sulfide.
8. Composition according to claim 1, wherein the modified sulfur employed contains fillers, dispersing agents, emulsifiers, colorants, talc and/or inhibitors.
9. Polymeric compositions in the form of dispersions, of olefinic polymers obtained by radical polymerization or additive reaction in 10 to 90 percent by weight of sulfur which has been modified by means of plasticizers containing at least one thiophilic, nitrogen-containing viscosity regulator.
10. Compositions according to claim 9, wherein the olefinic polymer employed is polyethylene or polypropylene.
11. Compositions according to claim 9, characterized in that they contain 20 to 60 percent by weight of modified sulfur.
12. Compositions according to claim 9, wherein the thiophilic, nitrogen-containing compound employed is selected from the group consisting of amines, diamines, alkanolamines and amides.
13. Compositions according to claim 12, wherein the thiophilic, nitrogen-containing compound employed is present in amounts of up to 5 percent by weight based on sulfur.
14. A process for the production of a polymeric composition comprising the steps of: treating sulfur with at least one plasticizer and at least one thiophilic, nitrogen-containing viscosity regulator to produce a modified sulfur and dispersing an olefinic polymer in the modified sulfur.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT754977A AT349755B (en) | 1977-10-21 | 1977-10-21 | POLYMERIC COMPOSITIONS AND PROCESS FOR THEIR PRODUCTION |
| AT7549/77 | 1977-10-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US4240949A true US4240949A (en) | 1980-12-23 |
Family
ID=3597158
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US05/951,588 Expired - Lifetime US4240949A (en) | 1977-10-21 | 1978-10-16 | Polymeric compositions and process for their production |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4240949A (en) |
| AT (1) | AT349755B (en) |
| DE (1) | DE2844204A1 (en) |
| FR (1) | FR2406652A1 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4425262A (en) | 1981-02-20 | 1984-01-10 | Mitsui Toatsu Chemicals, Inc. | Electroconductive resin composition |
| US5264031A (en) * | 1991-12-23 | 1993-11-23 | Kerr-Mcgee Chemical Corporation | Particulate opacifying extender for polymer coatings |
| US5278208A (en) * | 1991-12-23 | 1994-01-11 | Kerr-Mcgee Chemical Corporation | Particulate opacifying extender for polymer coatings |
| ES2166691A1 (en) * | 2000-01-27 | 2002-04-16 | Catalana Del Paper S L | Procedure for the production of a lamina in plastic material with bubbles, for packaging and product obtained |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5962630A (en) * | 1997-12-03 | 1999-10-05 | The United States Of America As Represented By The United States Department Of Energy | Process and material that encapsulates solid hazardous waste |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3251797A (en) * | 1962-04-13 | 1966-05-17 | Thiokol Chemical Corp | Plasticized polyvinyl chloride compositions with polymers of sulfur and an unsaturated compound |
| US3290266A (en) * | 1963-04-15 | 1966-12-06 | Research Corp | Compositions containing elemental sulphur |
| US3299568A (en) * | 1966-03-01 | 1967-01-24 | Research Corp | Compositions plasticized with sulphur |
| US3450667A (en) * | 1966-06-10 | 1969-06-17 | Stauffer Chemical Co | Polymer compositions containing sulfur and process for preparing same |
| US3542701A (en) * | 1966-11-29 | 1970-11-24 | Shell Oil Co | Elementary sulfur as flame-retardant in plastic foams |
| US3634293A (en) * | 1968-08-31 | 1972-01-11 | Basf Ag | Compositions containing bitumen and an olefin polymer |
| US3676166A (en) * | 1970-09-28 | 1972-07-11 | Phillips Petroleum Co | Plasticized sulfur compositions |
| US4079023A (en) * | 1977-01-12 | 1978-03-14 | Chevron Research Company | Sulfur foam process and product |
-
1977
- 1977-10-21 AT AT754977A patent/AT349755B/en not_active IP Right Cessation
-
1978
- 1978-10-11 DE DE2844204A patent/DE2844204A1/en not_active Ceased
- 1978-10-13 FR FR7829255A patent/FR2406652A1/en active Granted
- 1978-10-16 US US05/951,588 patent/US4240949A/en not_active Expired - Lifetime
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3251797A (en) * | 1962-04-13 | 1966-05-17 | Thiokol Chemical Corp | Plasticized polyvinyl chloride compositions with polymers of sulfur and an unsaturated compound |
| US3290266A (en) * | 1963-04-15 | 1966-12-06 | Research Corp | Compositions containing elemental sulphur |
| US3299568A (en) * | 1966-03-01 | 1967-01-24 | Research Corp | Compositions plasticized with sulphur |
| US3450667A (en) * | 1966-06-10 | 1969-06-17 | Stauffer Chemical Co | Polymer compositions containing sulfur and process for preparing same |
| US3542701A (en) * | 1966-11-29 | 1970-11-24 | Shell Oil Co | Elementary sulfur as flame-retardant in plastic foams |
| US3634293A (en) * | 1968-08-31 | 1972-01-11 | Basf Ag | Compositions containing bitumen and an olefin polymer |
| US3676166A (en) * | 1970-09-28 | 1972-07-11 | Phillips Petroleum Co | Plasticized sulfur compositions |
| US4079023A (en) * | 1977-01-12 | 1978-03-14 | Chevron Research Company | Sulfur foam process and product |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4425262A (en) | 1981-02-20 | 1984-01-10 | Mitsui Toatsu Chemicals, Inc. | Electroconductive resin composition |
| US5264031A (en) * | 1991-12-23 | 1993-11-23 | Kerr-Mcgee Chemical Corporation | Particulate opacifying extender for polymer coatings |
| US5278208A (en) * | 1991-12-23 | 1994-01-11 | Kerr-Mcgee Chemical Corporation | Particulate opacifying extender for polymer coatings |
| ES2166691A1 (en) * | 2000-01-27 | 2002-04-16 | Catalana Del Paper S L | Procedure for the production of a lamina in plastic material with bubbles, for packaging and product obtained |
| ES2166691B1 (en) * | 2000-01-27 | 2004-05-01 | Catalana Del Paper, S.L. | PROCEDURE FOR THE MANUFACTURE OF A SHEET IN PLASTIC MATERIAL WITH BUBBLES, FOR PACKING AND PRODUCT OBTAINED. |
Also Published As
| Publication number | Publication date |
|---|---|
| ATA754977A (en) | 1978-09-15 |
| FR2406652A1 (en) | 1979-05-18 |
| DE2844204A1 (en) | 1979-04-26 |
| AT349755B (en) | 1979-04-25 |
| FR2406652B3 (en) | 1981-06-26 |
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